


Dude Looks Like A Lady

by BrieflyMaximumPrincess



Category: Supernatural
Genre: Boys Kissing, Boys in Skirts, Corsetry, Crossdressing, Lucifer in Heels, Lucifer in Makeup, Lucifer in a Dress, M/M, Makeup, Punk Lucifer (Supernatural), Trans Character, Trans Hannah, Trans Raphael, makeout
Language: English
Status: Completed
Published: 2018-08-03
Updated: 2018-08-03
Packaged: 2019-06-21 03:03:21
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,577
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15548163
Author URL: https://archiveofourown.org/users/BrieflyMaximumPrincess/pseuds/BrieflyMaximumPrincess
Summary: Lucifer lost a bet and his friends can play doll with him for the evening. Sam looks as Raphael and Hannah dress him in girl clothes and he can't say he doesn't like it.





	Dude Looks Like A Lady

**Author's Note:**

> Thank you to [YouCantKeepMeDown](https://archiveofourown.org/users/YouCantKeepMeDown/pseuds/YouCantKeepMeDown) who beta read this fic.

It was the end of the week and Sam took the habit to get a drink at that bar every Fridays. It may have a little to do with the fact that he knew who did the same and who would be there too. It was a nice bar where people came to chill, the music was nice and quiet, the sofas comfortable, the light dim. A perfect setting for a romantic date and Sam didn’t doubt it was full of couples on Saturday nights, but Fridays were less crowded.

That evening it was nearly empty, safe from him at the bar, and the group of people Sam took the habit to wave at but never really dared to go speak to, past a couple of words here and then. They were three, Raphael, Hannah and Lucifer. Sam couldn’t help but to feel a little impressed by them, especially by Lucifer, what made him stutter like an idiot once or twice as Lucifer was talking to him while ordering drinks.

It took time for Sam to realize that they were all the time the same three people. Because sometimes Hannah was Joe. They were the same person but it depended on their mood to be more like a woman or like a man. Then, Sam realized Rapahel was a transexual too. With her delicate feature and her elegant way to move, he would have never guessed she wasn’t born a woman. And then, there was Lucifer. With his bad boy attitude and his punkish look, he was surely the one who denoted the most in the chic set up of the bar, dragging his overused leather jacket and tore jeans on the rich fabrics and sipping on beers straight from the bottle when Raphael and Hannah drank fancy cocktails, like Sam did too.

That night, Raphael and Hannah had brought a lot of things with them. They had a suitcase full of clothes, open at their feet, toilets bags full of items they emptied piece by piece on the table, a hand mirror, sparkly jewels, and other little and fragile looking things Sam didn’t know the name of.

“You’re ready little doll?” Raphael asked looking at Lucifer.  
“Oh my my... What did I agree to?” Lucifer sighted, looking at the mess of objects on the table in front of him. Raphael batted his hand away from them.  
“Don’t put your paws on everything” she scolded him.  
“I’ll never look like a woman with a jaw that square. I’ll be ridiculous.”  
“A bet is a bet. You promised me I could play with you if you lost,” Raphael reminded him.  
“But I don’t want to look ridiculous all night long.” Lucifer whined.  
“Don’t worry sweetie, just a little bit of makeup magic trick and your mother won’t recognize you anymore. Let me work that,” Hannah said to put an end to his rant. “Haven’t you see me without my makeup on? It’s insane what a little contouring can do.”

Sam could agree on that. When they came to the bar in men’s clothes, Joe was nothing like Hannah. That’s why it took Sam so much time to figure out they were the same person.

“But before that, we should start by dressing you like a proper lady or you will ruin the makeup when you’ll put on the clothes.”  
“What do we go for? Real lady look or obvious drag queen?”  
“Do I have a say on that?” Lucifer asked with hope. “I don’t want to try on all of the clothes you brought tonight. I thought, you would have discussed that question together before.”  
“It’s not really on you to choose tonight. And Hannah and I thought you were joking the other day when you said you’d let us give you a make over for the night.”  
“We got excited and we brought everything we could put our hands on that might fit you.”  
“Are you going to bail on us?” Raphael taunted Lucifer.  
“I’m true to my words. Even if I start to seriously regret it.”

By the look on his face, Sam was sure it was true. He had no idea what about the bet he lost was, but time would surely pass before Lucifer dared to bet against his friends again.

“Let’s begin. Stand up!” Raphael commanded.

Lucifer executed the order, Raphael and Hannah doing the same to look at him and decide what they wanted to go for.

Sam was curious and didn’t fake to not take interest in their conversation. He sat looking away from the bar, sipping on his drink as he looked at them. Lucifer looked embarrassed to have all the eyes on him, but he winked to Sam anyway. Maybe he expected him to comment on what they were doing. But the only interruption came when the barmaid told them she didn’t want to have a naked man in the middle of her bar. For her, they could play doll all they wanted with Lucifer but if he had to change clothes, he would have to use the men’s room.

“Why the men’s room? If we make a lady out of him, can’t she use the ladies room?” Raphael pointed.  
“Same difference for me. I really don’t care what door he chooses to go through, as long as I don’t have a dick in the middle of my bar.”  
“Woh hey! I don’t plan to be naked in front of anybody. Are we clear?” Lucifer warned his friends.  
“Working attire or evening gown?” Hannah asked for Raphael’s opinion.  
“Personally, I’d like to see him in that blue dress,” the barmaid said.  
“No glitter!” Lucifer answered scandalized.  
“You promised we could do what we wanted.”  
“Still. No glitter.”  
“Alright,” Raphael sighted.

She circled around the blond man like a shark, pointing what she wanted to change on his appearance next. Hannah came closer to him from behind. Lucifer didn’t flinch until they put their hand on his crotch. He jumped and gasped at the sudden contact, folding over himself in a reflex of protection. Sam jumped in empathy too.

“Put that on,” Hannah said showing with her other hand a piece of fabric Raphael was holding for him. “It’s not that we don’t appreciate it but tonight, we don’t want to see that delicious bulge.”  
“It’s not ladylike,” Raphael remarked, far too serious next to a beaming Hannah.

Lucifer took the piece of fabric in hands as they let their grip go.

“I will never fit in this. It’s far too small.”  
“It’s the point. We want you to appear totally flat. So it must be tight to conceal… All of this,” they said moving their hands towards his crotch.  
“We never said it would be comfortable,” Raphael added. “Also, you have hips.”  
“Like every other human beings, I suppose.”  
“What I mean by that is that I’m sure we can get a narrow waistline out of you.”  
“Oh my God yes!” Hannah clapped excited.  
“I fear the worst.”

Raphael rummaged in the suitcase for a minute before she fished something out of it.

“Let me introduce you to the ultimate torture device: the corset!”  
“No,” Lucifer said categoric.  
“Yes!” Hannah bounced in excitement, making Sam smile.  
“You promised,” Raphael reminded him.  
“Alright,” Lucifer surrendered.  
“Take a big breath and suck it up, Rose DeWitt Bukater.” Hannah laughed as Lucifer walked to the men’s room.

Raphael and Hannah put a hand on each one of his shoulders and he switched direction obediently, towards the ladies room, resigned.

“They are having a lot of fun,” the barmaid said to Sam.  
“I’m kinda curious to see how he will look once they have finished with him.”  
“You’re into this?” She asked him.  
“I… I don’t know. I always thought Raphael and Hannah were impressive.”  
“And you always liked Lucifer a lot, don’t you?” The barmaid said, winking at him as she put a new drink in front of him.

A little cry came from the ladies room. Nothing really alarming. Sam’s imagination was running wild at the thought of what was happening in there. His dick twitched at the idea of them putting Lucifer in that pretty corset and pulling on the laces.

When they came back to the main room, Hannah presented their work proudly and Sam had to swallow hard. Lucifer had curves. It was stunning to see how his body looked different. They surely took advantage of him agreeing to play doll seeing how tight they made the corset under the long and tight dark dress he had put on.

“Fuck it hurts. It’s like I can’t breathe fully. You wear that everyday?”  
“I don’t but she does,” Hannah pointed to Raphael.  
“I don’t make it that tight though. I need to do things all day long. Beside, we may had go a little rough on you. But it’s not everyday we can put you in a dress.”

Once they sat again, Lucifer steeper than usual, they argued on the choice of jewels and Hannah gave Lucifer a pair high heels he laughed at but put on willingly.

Then, they were busy for a rather long time with the makeup. It was interesting how those creams and products rubbed off Lucifer’s traits to make him look totally different. Even if Sam liked the original version a lot, he couldn’t say Lucifer wasn’t pretty like this. Foundation made his face look flawless, even erasing that little mole on his cheekbone. His eyes appeared in an insane deeper shade of blue. Sam caught himself staring.

Raphael ended by putting some alarmingly red lipstick on Lucifer’s lips while he obediently looked up to her with eyes too innocent to not give Sam some nasty ideas. His usually thin lips looked full and Sam wondered how they’d taste.

His thoughts wandered elsewhere, picturing the sight Lucifer would make with the same expression he had on his face while looking up at Raphael. The difference being that in Sam’s mind, Lucifer would be on his knees in front of him instead, those pretty red lips parting to swallow his cock.

Once Raphael had finished, she kissed the tip of Lucifer’s nose. He crooked it, and Sam smiled to himself at the idea that he could find Lucifer adorable doing this. Lucifer reciprocated by kissing the void as Raphael and Hannah took a step back to look at their work.

“Do we want a wig? Long hair?”  
“No, I like the spiky blond hair. Let’s keep him that way.”  
“You meant ‘her’, I’m sure,” Hannah said.  
“The most polite would be to ask the principale protagonist about that. So Lucifer, what would it be for tonight? He or she?” Raphael asked as she guided Lucifer to stand in front of a wall mirror.

He looked at himself for a moment, turning a little to one side then to the other to inspect his clothes and his general look, confusion painting on his face.

“I don’t know. I feel so hidden under all of this. I know I’m in front of that mirror but I don’t see myself in it. It’s kinda weird.”  
“Let’s have an outside opinion. Hey Sam, what do you think of our little doll?” Hannah asked him.

Sam knew perfectly what Lucifer usually looked like. He saw the entire makeover happening. But when Lucifer turned to show him the result, hope in eyes that never appeared this much blue before, Sam couldn't find his words. He felt warm in his lower belly.

“See, I look perfectly stupid.”

Was it disappointment in Lucifer’s voice? Sam could not let that happen. He couldn’t bare to see Lucifer this pretty but this sad at the same time. Not knowing what to say to show him the effect he had on him, Sam settled for something he would normally never do. But again, Lucifer normally didn’t look like this either.

Sam finished his drink in one go to find courage and walked like a predator towards Lucifer. This one recoiled seeing him coming his way and tried to step back but the high heels weren’t playing on his team and he stumbled a little. Sam caught him by the waist and plastered him against his body, feeling Lucifer shift under his grip. The feeling of his body against his wasn’t what Sam expected. Lucifer had lady’s forms but under Sam’s touch his body was only hard lines because of the corset under the dress. Sam pressed closer and whispered in a husky voice.

“You’re driving me crazy. I want to kiss those pretty red lips and then take you to a dark corner to help you out of that dress. You can keep the rest on, though. I want to ravage that pretty lipstick, smear it all over your mouth and chin by kissing you. Then, I want to bend you over and make you scream my name while you cum.”  
“Oh shit.”  
“Can I have a kiss?” Sam asked in the same gravel voice.

Lucifer didn’t answer with words. He put his hands on each side of Sam’s face and kissed him roughly. Sam supposed Lucifer tried to stand up but he tripped over his own foot again and lost completely his balance. He would have fallen if Sam didn’t hold him in place.

Sam wanted to take Lucifer a little away from his friends who were losing their cool, clapping, cheering and laughing at them. But Lucifer was definitely unable to walk on high heels. Sam had to help him by lifting him awkwardly in his arms. Hannah went positively crazy seeing this. Lucifer was heavier than what Sam expected and they landed on a sofa closer than what Sam would have wanted. It would do though, because Sam couldn’t wait anymore to feel Lucifer’s hard line body against his.

They made out like horny teenagers alone in a house, except the fact that they weren’t. Lucifer’s friends were commenting every move. Sam could just hear a blur of voices though because all his attention was on Lucifer. He slid a hand under Lucifer’s dress, lifting it up on his tight, and roamed his hand on what Lucifer was wearing under. He was beautiful, unusual, and Sam liked it more than he probably should have. As for Lucifer, it was surely turning him on more than what he would have thought when he lost that bet as he was reduced to making all sort of pretty noises Sam would never have imagined the Lucifer he knew could do.

“Take a room! You are not in that sort of establishment!” The barmaid shouted scandalized at them.  
“Let’s go to my house. You’re making me hard,” Sam proposed between two kisses. Lucifer nodded frantically.

Sam and Lucifer were going away under Raphael and Hannah’s catcalls and wishes for a successful fuck when Sam trotted back to them to ask for Raphael's lipstick. She looked at him with a judging glare while giving it to him, more amused than she wanted to admit.

“I like it,” Sam explained with a twisted grin as he came back to Lucifer and slapped his rear gently to make him exit the bar.

The next day, when Sam and Lucifer met Hannah and Raphael for lunch, they were late. Though the ladies were classy enough to not ask why. They had little doubts about it. Lucifer was wearing red lipstick again and Sam had some on the collar of his shirt.

**Author's Note:**

> [Dude looks like a lady](https://youtu.be/nf0oXY4nDxE) by Aerosmith.


End file.
